10 Lessons from 10 Startup Weekends

If you know me or have read anything from my blog, it’s probably abundantly obvious that I love hackathons and am particularly fond of Startup Weekend. Well, on August 18, I wrapped up my 10th Startup Weekend. I have a bunch of half-written blog posts sitting with reflections on my experiences and learning from these various events. However, with the tenth, I thought it would be fun to pick one thing I’ve learned from each event and do a kitschy 10-things post. There’s nothing really novel here, but I think those who have been to Startup Weekend will be able to relate and hopefully those who haven’t will be convinced to attend.

1. January 2012, “Rise of the Designer” Theme, Seattle, WA

What’s the right size for a team? This was the first time I had ever attended Startup Weekend and the biggest lesson from this event was that a bigger team doesn’t necessarily produce better results. The team I joined at this event ended up with 14 members and a leader who, while a great guy, was not ready to manage the challenges that arise when 14 people meeting for the first time and spend 54 hours in a high-pressure environment trying to deliver on a novel vision. The more people on a team, the more opinions there are, meaning the more prepared and willing the leader needs to be to manage it all. The team had some strong personalities that resulted in a lot of unproductive argument. Naturally, team size isn’t an issue in isolation. Team productivity is the net of all the unique personalities that comprise it, the structure placed around its operation, and numerous environmental factors. It’s important to choose teammates based on criteria that matter to you. Personally, I prioritize people I’d enjoy working with, who are aligned in what they want to achieve, and who have complimentary skills. I look for leadership that is willing to make unpopular decisions and follow through. It’s not always comfortable, but it’s often required to get things done on a tight timeline.

2. April 2012, “Government” Theme, Seattle, WA

Are you asking the right questions? After my first Startup Weekend experience, I was determined to (1) be part of a moderately-sized team and (2) play a leadership role. Before the initial idea pitches, I canvased the room to gather support for the idea I wanted to work on. Fortunately, things worked out. My idea was selected and I had the opportunity to lead a team. In bringing the team together, I was intentional about keeping it at no more than 6 people with a balanced set of skills. With a solid team in place, I focused my attention on putting customer development to practice. On the upside, I learned a lot about interviewing potential customers. On the downside, I spent way too much time putting together a survey. But I did learn a lot about how to tailor survey questions to produce meaningful data while avoiding inadvertent manipulation of the respondent’s responses. The key is to ask behavior-based questions that are indicative of users’ pre-existing behaviors. Making sure questions solicit objective responses ensures that we gather facts rather than supposition and speculation. If we must ask a subjective question, it helps to be aware of psychological influences like anchoring, etc. A great book on the topic of psychological influences is Influence: The Psychology of Persuasion

3. May 2012, General Event, Seattle, WA

What’s a mentor? At this event, I was again in charge of a survey to collect customer data. However, what I learned this go-around was far different from what I learned at the prior event. To gauge whether the survey content would help achieve our goals, I ran it by several event mentors. Each time I spoke with a mentor, the feedback was essentially to rewrite the entire survey. So after each conversation, I would go back and spent over an hour hour carefully crafting a revision. When I got the same feedback a fourth time, I realized I was spinning in circles and that the information I wanted to capture was pretty well covered by the original rendition of the survey. This was the first time I had experienced “mentor whiplash”. When getting feedback from mentors, it’s important to remember that mentors are there to give guidance, not instruction (it’s good for mentors to remember this too!). We shouldn’t necessarily spin on our heels just because someone we deem as credible suggests that we’re going down a wrong path. Usually, better decisions come from seeking out feedback from relevant individuals, internalizing their feedback, and making our own decisions.

4. July 2012, “Women’s Edition” Theme, Seattle, WA

Have you ever walked in a room and been the only woman/man/adult/child/foreigner/student/whatever? If you haven’t, it’s an experience I’d recommend. The Women’s Edition of Startup Weekend inverted the typical male-to-female participant ratio to encourage and inspire women, who are typically less well-represented at hackathons. For this event, the balance of participant gender was set at about 85% women and 15% men. Although I have long believed in the importance of supporting and being inclusive of minority groups, I don’t know that I’ve ever had an experience that made me more acutely aware of being on the other side of the table. It’s one thing to put yourself in that position by choice, for example through intentional selection of friends. It’s something else completely when being a minority is entirely outside your control. I still remember the feeling of walking into the room where things were kicking off and instantly being struck by uncertainty, self-awareness, self-doubt, and a wave of other emotions. This was an eye-opening experience that has helped me to empathize with what minorities go through on a daily basis. It’s up to everyone to choose how they address diversity and minorities, but at a minimum, I think it’s important for everyone to be cognizant of what others experience.

5. September 2012, General Event, Seattle, WA

What do you do when things look dire? I attended this event with a close friend and while we didn’t have a particular idea we wanted to work on, we knew we wanted to work together. Most of the ideas that were selected either weren’t that appealing to us or ended up with teams to which we didn’t think we’d add net value. One of the ideas that was chosen ended up without any team members aside from the person who pitched it. We found the idea somewhat interesting, so we decided to form a small, three-person team. We felt that this team size was an opportunity to get a more realistic experience of what it’s like to be a co-founder. Like real founders, we certainly experienced plenty of ups and downs throughout the weekend (of course, all in a safe, low-stakes, low-risk, time-boxed environment). There were multiple times when we’d asked ourselves why we even bothered continuing with the weekend. We even hit one of these troughs around 5 hours before final presentations. But we pushed through, despite the tight deadline and the continual need to tweak or scrap the business model as we got feedback from potential customers. During the final presentation Q&A, one of the judges literally, word-for-word, told us we were “full of shit”. But compared to what we’d been through the rest of the weekend, the words didn’t phase us for a moment. It was actually great feedback… how can a tiny team possibly deliver on a big vision? Then again, we had persistence on our side.

6. November 2012, General Event, Kirkland, WA

What do you want to achieve? Having worked on a lot of serious projects at previous events, I was eager to work on something (1) fun and (2) hardware-related at this event. I pitched “SlapBot”, a robot that slaps you when you send annoying or mundane tweets and Facebook posts. This quickly becameZapBot, which would give an electric jolt instead of a slap. Although the idea didn’t get enough votes to officially become a project, there was interest from two other participants, so we formed a 3-person rogue team. The initial intent was purely to be a joke and to have fun, but the novelty of the gadget and the positive response from people we showed shifted the tone of our conversations toward evaluating the concept as a serious business. Unfortunately, this resulted in a final pitch was neither funny nor compelling as a business opportunity. It’s important to know your objective, then tailor your actions and train your focus on achieving it. Understand the experience you need to be delivering and deliver on it. Be wary of shiny distractions. I later completely revised the pitch to focus on the humorous side of the concept and presented again in a different context. The second time around, the result was exactly what I had hoped for – lots of laughter and delighted conversation.

7. November 2012, General Event, Seattle, WA

When was the last time you let your hair down? After building a silly device like ZapBot, I was ready to get back to business. I had an idea I thought would be interesting and that might have a business behind it. But then someone jokingly pitched “Cartar”, a keytar for jamming in the car. I was hooked. Try as I might, I couldn’t get the person who pitched the idea to work on it. So, I did what any good entrepreneur would do. I stole the idea (with his permission) and formed another rogue team. From the first night, I started dreaming up what the final presentation would look like. I wanted it to be an experience rather than a presentation – something people would remember. I also wanted our team to have a blast working on the project. Keeping those goals front-of-mind through the weekend, both were achieved in spades. I knew it was a success when one of my teammates, who had been to numerous Startup Weekends in the past, told me that this one was the most fun he’d ever had. I knew we’d delivered on the presentation (1) when Rich Barton, a special guest, stopped looking at his phone to watch our presentation, and (2) when the audience gave us a roaring ovation, the longest I’ve yet seen at a Startup Weekend. I wouldn’t say there was a great business case for the product, but I will say with confidence that we truly captured the potential of what the Startup Weekend experience can be. And all because we focused on having a great time.

8. January 2013, Special University of Washington Event, Seattle, WA

What is a leader and what do they do? At this event, I joined a team comprised entirely of students, non of whom had been to a Startup Weekend before or had any industry or entrepreneurial experience. To be clear, there’s a lot of potential for mischaracterization in that statement. These students were incredible. I’ve met professional programmers who can’t program as well as the budding engineers who were on this team. I’ve also met business people who get locked up in over-analysis instead of making things happen, the way the other members of this team did. But experience is experience and that was the one thing they were lacking. It was clear very early on that this was leading to some decisions that would have led the team down an unproductive path. At that point, it would have been easy to have stepped in and forcefully grabbed the reins to pull things in a different direction. However, this was one case in which it was especially important not to see anyone on the team discouraged. So instead of being direct, I tried encouraging discussion and helped guide conversations down a reasoned path, advocating the collection of data where knowledge gaps existed. This approach worked well as the team didn’t hit the bumps and pitfalls first-time Startup Weekenders usually go through. More importantly, everyone left with a solid experience under their belts and eager to participate again in the future.

9. April 2013, General Event, Portland, OR

What are the rules about rules? Once again, I went rogue. I knew I wanted to work on something hardware related, but the idea I pitched didn’t get picked and neither did the one other hardware project I was interested in (there were a total of three hardware ideas pitched). At this point, I’d had some experience going rogue before, so this time I had a pretty good idea of what I was doing. After it was obvious that my idea and the other one I was interested in weren’t going to get enough votes to be selected, I grabbed the other person and we recruited two more people with complementary skills. The event organizers were surprised when we registered our team with an idea that hadn’t been officially selected, but nothing really forbade this. With warnings of risk and votes of no-confidence, we proceeded with the usual paces, identifying and validating a promising market opportunity, building a solid prototype, and bringing it together with a strong presentation. This might have happened if we had gone along with what we were “supposed” to do, but we were all really glad we took the route we did. Given the choice of betting on luck or betting on myself, I’d choose myself. Rules are designed as constraints, but they’re uni-dimensional in a multi-dimensional world. Shifting one’s view opens up new possibilities that aren’t immediately obvious.

10. August 2013, General Event, Seattle, WA

How much does team composition really matter? Many of the most important lessons I’ve learned at the various Startup Weekends I’ve participated in have to do with team. It just so happens that the most important lessons I’ve learn as a Startup Weekend organizer have also been team-related. At the most recent Startup Weekend I participated in, I had the great fortune of connected with someone who’s skills complemented my own in an it’s-too-good-to-be-true kind of way. As we talked about our areas of interest and backgrounds, lightening struck, followed by immediate clarity. There was no doubt that we were the basis of an ideal team to work on one of the project we had in mind. While other participants weren’t particularly interested in working on the idea, we convinced two talented friends of mine, who were actually simultaneously event organizers, to join the team. The result was an incredibly productive weekend that ran like clockwork. Everyone pretty much knew exactly what to do and got right to it. I think we were all pretty amazed with what we were able to accomplish in such a short timespan, but in retrospect it made sense. We were set up for success from the outset by forming a well-balanced team.

It’s been a long journey since my first Startup Weekend, but looking back, I couldn’t be more pleased with the amazing friends I’ve made, the knowledge I’ve gained, and the seriously cool stuff I’ve helped build. Startup Weekend doesn’t begin to compare to actually founding and running a startup, but there’s no question that the experiences it’s offered will be a major contributor to any success I’m fortunate enough to have.

There are a ton of people to thank for all these incredible experiences, but the list would go on forever. You know who you are – thank you all for teaching me so much!